On my '05 Ultra Classic the front brake will bleed down after sitting overnight. Immeditely after starting there will be zero brake unless I 'pump up' the brake by squeezing the lever about a dozen times. Once I do that, it is fine for the remainder of the day. The m/c fluid level has not changed. Does this sound more like a master cylinder issue or one pertaining to the front caliper?

 

Air is getting in somwhere!
Do yourself a favour and get it serviced!

 

If the fluid level isnt changing and you cant find leaks anywhere, then I'm thinking youve got air in the system. Bleed the whole front real good starting with the caliper furthest away from the master, then zip tie the lever to the grip overnight. If the lever pressure is gone in the morning, time for a master cylinder rebuild. If its still there, you got all the air out. Good luck!

 

I will give the bleeding a try this weekend and post back the results. Thanks!

 

You have a bad front brake master cylinder is what it sounds like to me.
It is a pretty common issue on these bikes front what I have found. In February this year, we bought a 2012 FXDC for the Wife. This bike was brand spanking new with 2 miles on the ODO.

Rode it home that night and the next morning I go to roll it out of the garage to take it for a spin. I go to grab the front brake and there is no brake, ZERO front brake and the lever falls all the way to the grip.
So I pump it up and I have brakes now. I ride to the dealer and they had to replace the front master cylinder. Service manager tells me it is one of the more common issues they see on a daily basis. They do so many of them, they stopped doing rebuild kits and just keep new masters on the shelf for quick replacement.

 

I have what I think is a very similar issue. I simply dont have much brake pull having to pull back the lever almost all the way to the bar before they would stop. I was not losing any fluid anywhere.....I bleed the system multiple times only to have the same result. In the end, here is what was wrong

Take the calipers off and shoot brake parts cleaner in the pistons. What was happening is my stock pistons were not retracting back to the start position due to them sticking on the cylinder. Once I freed up the pistons to move easily in the cylinder my full brake handle resistance was like brand new again. Now the continued issue is that you will have to do it semi regular. I did mine 2 years ago, and they are back like they were again. Hope this helps.